Director, Customer Strategy & Operations

Your Core, Our DNA: High Velocity. High Intensity. High Trust. High Expectations. High Impact.

FutureFit AI could be the right next step in your career journey if reading those words resonate deeply for you, full stop. You live and lead with bold humility, pursue audacious goals, and are motivated by having a meaningful and positive impact on the people and the world around you.

The Role

First, an important note: data shows that men on average apply for a role if they meet 3/10 requirements while women often only do so if it’s 10/10. We work hard to be clear and specific about what our roles include and demand and encourage you to apply if you see a strong (but not necessarily perfect) fit between you and the opportunity.

You will own a portfolio of high-priority customers and be accountable for their success with our platform and the retention and expansion of their contracts. You will be asked to:

  • Own the end-to-end customer lifecycle from pre-close of sale through to implementation, ongoing support, and renewal and expansion. You will develop a comprehensive success strategy for each customer and deliver success at each stage of the partnership with support from team members across functions, including CS, Growth, Product, and Engineering.

  • Be a strategic leader for your customers to help them achieve their objectives while using our platform, whether they are looking to promote job seeker upskilling and employment, create capacity for workforce staff, help employers address talent shortages, or build more collaborative workforce ecosystems. Your customers' success will be used to develop case studies and best practices for success with other FutureFit AI customers.

  • Navigate and support a complex set of stakeholders at each customer to ensure ongoing satisfaction, sustainability, and expansion of the partnership. You will be the lead point of contact with project teams, executive sponsors, and the diverse set of partners that engage with our platform, including workforce service providers, government agencies, employers, training providers, and more.

  • Contribute to FutureFit AI's product roadmap and domain expertise through a deep understanding of current and future customer requirements. Your insights will help us build a better product and contribute to more effective workforce systems.

  • Serve as a leader for the Customer Success team, mentoring more junior team members, helping build scalable CS processes and systems, and supporting the Head of CS and COO in developing a replicable success strategy across customers.

Note that this role will be based out of our US headquarters in New York City. We will only be considering candidates who are currently based in close proximity to New York City or willing to relocate in the immediate term, as we have a hybrid model and typically co-locate in person 2-3 days per week.

Your Experiences

You likely have two or more of the following work experiences: 

  • Management consulting

  • Utility player at a technology and/or impact start-up of <100 team members

  • Workforce development experience

  • Customer success or sales experience

Your Skills

  • Relationship management -  Proficiency: 5/5

  • Rapid & rigorous thinking & problem-solving - Proficiency: 5/5

  • Oral communication (leading meetings with stakeholders) - Proficiency: 5/5

  • Project management - Proficiency: 5/5

  • Strategic planning - Proficiency: 4/5

  • Navigating difficult conversations - Proficiency: 4/5

  • Presentation development - Proficiency: 4/5

  • Data analysis & manipulation - Proficiency: 3/5

Your Education

We don’t think degrees should block talent from finding pathways to opportunity and so this won’t be a factor in how we look at candidates. We do care that you are naturally curious, constantly learning, have overcome hurdles/challenges, and have a good handle on your strengths and gaps.

Job Benefits

  • Work directly with the founding team

  • Unlimited PTO

  • Health care

  • 401(K)

  • Career Development Budget

  • Technology reimbursement

  • Flexible schedules built on trust


This role will be based in New York City. Some days we work from home but everyone typically comes to the office at least a couple of times per week for face-to-face collaboration and team building.


The base salary range for this role is $110k-$140k plus equity; it is variable based on applied experience and other factors identified by the hiring committee.

Hiring Journey

At FutureFit AI, we believe in designing intentional and rigorous hiring journeys to help you determine if this is the best role and organization for you, based on your unique skills, mindset, and experiences. We operate at high velocity with high intensity and want an accurate taste of what that feels like before you get through the door. 

Every hiring journey at FutureFit AI consists of thoughtfully crafted steps including a performance challenge and rounds of interviews with team members. For this role, that might look like:

  1. Online Application

  2. Initial Screen/Checkpoint

  3. Performance Challenge and Debrief

  4. Final 1:1 Interviews

  5. Final Decision

Generally, this entire process takes around 4 weeks, although the timing can vary due to specific candidate circumstances.

Our Company

In looking at a job posting, it’s often hard to get a basic picture of the company profile (size, stage, structure, etc) which is why we are sharing it with you upfront. This helps you quickly decide and helps us focus any time we spend together on going beyond the basics:

  1. Problem Domain: Future of Work / Workforce Development - important that the problem domain interests you even if you haven’t worked in the space before

  2. Industry: SaaS / AI - technology and data are at the core of what we build 

  3. Customers: We partner with governments and workforce development organizations in much of our work and are increasingly working with employers / enterprises as we grow

  4. Structure: We are organized around the following key portfolios: Growth, Customer Success, Product, Engineering, Data, People & Culture, Finance & Operations

  5. Team: We are a team of 30-50 across US and Canada with main hubs in New York and Toronto

  6. Funding: We built the company from 0 to 1 with no external capital (a rare feat for tech startups) and have subsequently raised one round of funding led by JP Morgan which fueled a significant growth trajectory in 2022 for us

Our Core Principles

  • Be Curious 

  • Drive to Outcomes 

  • Raise the Bar

  • Speed Matters

  • Own It

  • We Over Me

About FutureFit AI 

At FutureFit AI, we’re on a mission to unlock pathways between talent and opportunity using the power of AI. We focus on personalized, AI-powered career guidance for job seekers, emphasizing skills over extensive resumes, and partner with workforce development partners, governments, and employers to level access to opportunity.

FutureFit AI is a growing, venture-backed company focused on using technology to improve the lives and outcomes for people going through career transitions. We’re a small, driven team, united by our commitment to the job seekers and workforce ecosystems we serve. We're not just building a company; we're shaping the future of work.

We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request an accommodation.

© FutureFit AI All rights reserved, we are proud to be an equal opportunity workplace. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, religion, color, gender identity, sexual orientation, age, disability, veteran status, or other applicable legally protected characteristics. We encourage people of different backgrounds, experiences, abilities, and perspectives to apply.

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